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Mass Spectrometry of Ionic Liquids: ESI-MS/MS Studies
Corresponding Author(s) : Kesharsingh J. Patil
Asian Journal of Chemistry,
Vol. 25 No. 15 (2013): Vol 25 Issue 15
Abstract
Herein, we reported our studies related to structural elucidation and gas-phase fragmentation patterns of the imidazolium and pyridinium based ionic liquids, using a positive ion electrospray ionization triple quadrupole mass spectrometry. Ionic liquids mainly imidazolium/pyridinium/alkylammonium salts, possess properties due to which there are many applications from the point of view of green chemistry. The recorded mass spectral patterns are presented and possible pathways for fragmentations are suggested. The mass spectrum of tetrabutylammonium bromide and its fragmentation pattern is discussed since we used this compound as a template in the synthesis of ionic liquids. Our analysis also suggests possibilities of associations of ions in the form of C2A+ species in vapour phase for the studied ionic liquids.
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- (a) P. Hapiot and C. Lagrost, Chem. Rev., 108, 2238 (2008); (b) C.S. Santos, S. Rivera-Rubero, S. Dibrov and S. Baldelli, J. Phys. Chem. C, 111, 7682 (2007).
- R.J. Soukup-Hein, M.M. Warnke and D.W. Armstrong, Ann. Rev. Anal. Chem., 2, 145 (2009).
- (a) M. Weishi and H.C. Tak, Acc. Chem. Res., 39, 897 (2006); (b) F.V. Rantwijk and R.A. Sheldon, Chem. Rev., 107, 2757 (2007); (c) J. Dupont, R.F. De-Souza and P.A. Z. Suarez, Chem. Rev., 102, 3667 (2002); (d) V.I. Parvulescu and C. Hardacre, Chem. Rev., 107, 2615 (2007).
- B.L. Ackermann, M.J. Berna, J.A. Eckstein, L.W. Ott and A.K. Chaudhary, Ann. Rev. Anal. Chem., 1, 357 (2008).
- S.J. Blanksby and T.W. Mitchell, Ann. Rev. Anal. Chem., 3, 433 (2010).
- J.C.A. Wuilloud, S.R. Gratz, B.M. Gamble and K.A. Wolnik, Analyst, 129, 150 (2004).
- H. Moriwaki, H. Harino, T. Yoshikura, T. Ohe, H. Nukaya, Y. Terao, H. Sawanishi, K. Wakabayashi, H. Miyakoda and J.-F. Alary, J. Environ. Monit., 6, 897 (2004).
- T. Gruendling, S. Weidner, J. Falkenhagen and C.B. Kowollik, Polym. Chem., 1, 599 (2010).
- (a) O. Bortolini, M. Bottai, C. Chiappe, V. Conte and D. Pieraccini, Green Chem., 4, 621 (2002); (b) B.L. Ackermann,A. Tsarbopoulos and J. Allison, Anal. Chem., 57, 1766 (1985); (c) Z.B. Alfassi, R.E. Huje, B.L. Milman and P. Neta, Anal. Bioanal. Chem., 377, 159 (2003); (d) P.J. Dyson, I. Khalaila, S. Luettgen, J.S. Mclndoe and D. Zhao, Chem. Commun., 2204 (2004); (e) J.H. Gross, J. Am. Soc. Mass Spectrom., 18, 2254 (2007); (f) G.P. Jackson and D.C. Duckworth, Chem. Commun., 522 (2004); (g) J.H. Gross, Mass Spectrometry; A Textbook, Springer-Verlag; Berlin Heidelberg, edn. 2, pp. 314-318 (2011); (h) A. Lesimple, O. Mamer, W. Miao and T.H. Chan, J. Am. Soc. Mass Spectrom., 17, 85 (2006); (i) P.J. Dyson, J.S. Mclndoe, D. Zhao, Chem. Commun., 508 (2003); (j) J.H. Gross, J. Am. Soc. Mass Spectrom., 19, 1347 (2008).
- G.A. Jeffery and R.K. Mcmillan, Progr. Inorg. Chem., 8, 43 (1967).
- W.Y. Wen, Water and Aqueous Solutions: Structure, Thermodynamics and Transport Processes, Willey Interscience, New York (1972).
- H.G. Hertz and M.D. Zeilder, Ber. Bunsenges. Phys. Chem., 68, 821 (1964).
- G.R. Gupta, G.R. Chaudhari, P.A. Tomar, G.P. Waghulade and K.J. Patil, Asian J. Chem., 24, 4675 (2012).
- (a) W.Y. Wen, K. Miyajima and A. Otsuka, J. Phys. Chem., 75, 2148 (1971); (b) K. Patil and G. Mehta, J. Chem. Soc. Faraday Trans. 1, 84, 2297 (1988); (c) K. Patil and G. Mehta, J. Chem. Soc., Faraday Trans. 1, 83, 2467 (1987); (d) M. Holz and K.J. Patil, Ber. Bunsenges. Phys. Chem., 95, 107 (1991).
- J. Dupont and P.A.Z. Suarez, Phys. Chem. Chem. Phys., 8, 2441 (2006).
- H. Li, J.A. Boatz and M.S. Gordon, J. Am. Chem. Soc., 130, 392 (2008).
- (a) J. Dupont, J. Braz. Chem. Soc., 15, 341 (2004); (b) Z. Meng, A. Dolle and W.R. Carper, J. Mol. Struct.(Theochem.), 502, 119 (2002).
References
(a) P. Hapiot and C. Lagrost, Chem. Rev., 108, 2238 (2008); (b) C.S. Santos, S. Rivera-Rubero, S. Dibrov and S. Baldelli, J. Phys. Chem. C, 111, 7682 (2007).
R.J. Soukup-Hein, M.M. Warnke and D.W. Armstrong, Ann. Rev. Anal. Chem., 2, 145 (2009).
(a) M. Weishi and H.C. Tak, Acc. Chem. Res., 39, 897 (2006); (b) F.V. Rantwijk and R.A. Sheldon, Chem. Rev., 107, 2757 (2007); (c) J. Dupont, R.F. De-Souza and P.A. Z. Suarez, Chem. Rev., 102, 3667 (2002); (d) V.I. Parvulescu and C. Hardacre, Chem. Rev., 107, 2615 (2007).
B.L. Ackermann, M.J. Berna, J.A. Eckstein, L.W. Ott and A.K. Chaudhary, Ann. Rev. Anal. Chem., 1, 357 (2008).
S.J. Blanksby and T.W. Mitchell, Ann. Rev. Anal. Chem., 3, 433 (2010).
J.C.A. Wuilloud, S.R. Gratz, B.M. Gamble and K.A. Wolnik, Analyst, 129, 150 (2004).
H. Moriwaki, H. Harino, T. Yoshikura, T. Ohe, H. Nukaya, Y. Terao, H. Sawanishi, K. Wakabayashi, H. Miyakoda and J.-F. Alary, J. Environ. Monit., 6, 897 (2004).
T. Gruendling, S. Weidner, J. Falkenhagen and C.B. Kowollik, Polym. Chem., 1, 599 (2010).
(a) O. Bortolini, M. Bottai, C. Chiappe, V. Conte and D. Pieraccini, Green Chem., 4, 621 (2002); (b) B.L. Ackermann,A. Tsarbopoulos and J. Allison, Anal. Chem., 57, 1766 (1985); (c) Z.B. Alfassi, R.E. Huje, B.L. Milman and P. Neta, Anal. Bioanal. Chem., 377, 159 (2003); (d) P.J. Dyson, I. Khalaila, S. Luettgen, J.S. Mclndoe and D. Zhao, Chem. Commun., 2204 (2004); (e) J.H. Gross, J. Am. Soc. Mass Spectrom., 18, 2254 (2007); (f) G.P. Jackson and D.C. Duckworth, Chem. Commun., 522 (2004); (g) J.H. Gross, Mass Spectrometry; A Textbook, Springer-Verlag; Berlin Heidelberg, edn. 2, pp. 314-318 (2011); (h) A. Lesimple, O. Mamer, W. Miao and T.H. Chan, J. Am. Soc. Mass Spectrom., 17, 85 (2006); (i) P.J. Dyson, J.S. Mclndoe, D. Zhao, Chem. Commun., 508 (2003); (j) J.H. Gross, J. Am. Soc. Mass Spectrom., 19, 1347 (2008).
G.A. Jeffery and R.K. Mcmillan, Progr. Inorg. Chem., 8, 43 (1967).
W.Y. Wen, Water and Aqueous Solutions: Structure, Thermodynamics and Transport Processes, Willey Interscience, New York (1972).
H.G. Hertz and M.D. Zeilder, Ber. Bunsenges. Phys. Chem., 68, 821 (1964).
G.R. Gupta, G.R. Chaudhari, P.A. Tomar, G.P. Waghulade and K.J. Patil, Asian J. Chem., 24, 4675 (2012).
(a) W.Y. Wen, K. Miyajima and A. Otsuka, J. Phys. Chem., 75, 2148 (1971); (b) K. Patil and G. Mehta, J. Chem. Soc. Faraday Trans. 1, 84, 2297 (1988); (c) K. Patil and G. Mehta, J. Chem. Soc., Faraday Trans. 1, 83, 2467 (1987); (d) M. Holz and K.J. Patil, Ber. Bunsenges. Phys. Chem., 95, 107 (1991).
J. Dupont and P.A.Z. Suarez, Phys. Chem. Chem. Phys., 8, 2441 (2006).
H. Li, J.A. Boatz and M.S. Gordon, J. Am. Chem. Soc., 130, 392 (2008).
(a) J. Dupont, J. Braz. Chem. Soc., 15, 341 (2004); (b) Z. Meng, A. Dolle and W.R. Carper, J. Mol. Struct.(Theochem.), 502, 119 (2002).